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Comment User dependent (Score 1) 542

I would say it depends on the sophistication of the company you are sending to. Are they small? They probably don't have IT staff and can't handle an SSH or VPN type transfer. Here you can use something like PGP web messenger or another third party securemail system that allows you to send messages that outside users can retrieve via an https secure site. If they are larger, you can work to get a technology like TLS enabled on your MTA and their's to encrypt from site to site. If they have an IT staff call them up and talk about the possibilities. They may support PGP. Or perhaps some other delivery method like an SSH sftp transfer.
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